On A Halloween Night
by AlElizabeth
Summary: Wee!Chester. Sam is 6, Dean is 10. Dean tells Sam the legend of Stingy Jack but assures his younger brother that its only a story... until they go out Trick-Or-Treating and find out that maybe it isn't a story after all.


Dean sat cross-legged on the motel bed, his back pressed up against the scratched headboard, both hands gripping a heavy, metal flashlight- the only source of illumination in the room- the beam shining up into his face to cast his eyes and cheeks in shadow.

Sam sat on his knees across from his ten-year old brother, practically vibrating with excitement.

It was Halloween night and Dean had promised to take him out Trick-Or-Treating.

But first, as the two boys waited for night to fall, Dean decided to set the mood with some scary stories.

"His name's Stingy Jack," Dean whispered, as though the moniker itself would summon its namesake, "And can never die. He walks around at night looking for anyone dumb enough to be wandering around in the dark."

Sam, bright-eyed, leaned forward to hear his sibling better. So far, Dean's stories hadn't been all that scary, just spooky so he thought nothing of inching closer to his brother.

"He wears an old, ratty cloak and keeps the hood up so you can't see his face," Dean continued, "And he carries a turnip with an ember in it from the Devil himself."

"A turnip?" Sam asked, incredulously.

"Yeah," Dean replied, "It's carved up and you can see the glow of that ember for miles and miles. It attracts people see? They want to get closer to it when they see it."

"Why not a pumpkin?" Sam asked, thinking of the pumpkins he'd helped carve in his classroom at school for the holiday.

"Because way back when Stingy Jack was around they had turnips," Dean answered matter-of-factly, "Shut up so I can tell the story."

"Sorry," Sam muttered but was quickly drawn into the tale.

"Anyway," Dean continued, "If you get close enough to him, he-"

"Why can't he die?" the six-year old interrupted again.

For a moment Dean scowled, irritated at having to stop again but then his eyes widened in realization.

"Oh yeah! Stingy Jack can't ever die because the Devil won't take him to Hell and he's too evil to go to Heaven."

Sam's eyes were round and almost as wide as Dean's.

"Why?"

The ten-year old hesitated, "Uh…"

"C'mon Dean," the six-year old pressed, "Why can't Stingy Jack die?"

"Because… Because he stole that ember from Hell and refused to give it back," Dean explained, once again back on track, "And so the Devil won't take him."

"He can't go to Heaven either because he wasn't a nice guy," Dean kept going, "He stole and hurt people and other bad stuff."

"Oh," Sam replied, "Okay."

Dean nodded, "So, if you get close enough to him and he pulls this big old coin out of his pocket and he asks you where you think you're going. Doesn't matter what you say, Stingy Jack will flip the coin and if it lands on heads, he'll kill you and you have to take his place in Heaven… but if it lands on tails, he kills you and you have to take his place in Hell."

Sam was leaning forward again, biting his lip.

"How does he kill you?"

Dean smiled; apparently he'd been waiting for this question.

"Stingy Jack puts his coin away, raises his hands to his hood, pulls it down and…. BOO!"

Sam, not ready for the sudden explanation, jumped back with a cry. Once he'd calmed a bit, Dean continued, "Some people say that since Stingy Jack is so old, he only has a skull for a head and others say he looks like a rotting corpse, with his skin peeling off his cheeks and maggots in his eyes."

The description seemed too much for the younger sibling and Sam frowned, inching backwards.

"But… But he's not real? Is he Dean?"

Deciding wisely that he'd rather not terrify his brother before they had to go out to get their candy, Dean quickly shook his head, "Of course not, Sammy. It's just a story."

Besides, the ten-year old thought, there are a whole lot more scarier monsters out there than Stingy Jack.

Glancing at the red glowing numbers on the bedside alarm clock, Dean reached over and turned on the lamp, bathing the motel room in a golden glow.

"Okay Squirt, looks like its time for us to get ready."

"YAY!" Sam shouted and jumped excitedly on the bed for a moment, landing on the floor, then freezing and peering over his shoulder at Dean still sitting on the mattress.

"Dean! I don't have a costume!"

The ten-year old though, was not worried. He knew that Sam didn't have a costume- that even if they'd asked their father to take them shopping for one John would have said no- but since Dean thought himself very clever he already had an idea.

Climbing from the bed, the older brother pulled the duvet down from the unused second bed- waiting for John's return- and yanked the white top sheet away from the fitted one. Dragging the sheet down the bed, Dean zipped open his duffel bag and grabbed a switchblade from underneath his clothes and cut two holes in the sheet.

With a flourish, Dean lifted the sheet and let it float down over Sam's head, his brother's hazel eyes peering out through the double holes cut into the fabric.

"There, you're a ghost."

Sam giggled happily. He raised his arms and made an 'ooOoo' sound.

Dean laughed, glad that his brother liked his makeshift costume.

"What are you going to be?"

Dean glanced down at his duffel bag, "I'll be… uh…"

He bent down and rummaged through his clothes, pulling out an oversized blue t-shirt with the Superman crest on the front that John had picked up from some thrift store they had stopped at when money was tight.

"I'll be Superman," Dean announced and pulled the large shirt over his head.

Now that the brothers had their costumes, Dean grabbed two pillows from the unused bed and pulled them out of their cases. Handing one pillowcase to Sam, the ten-year old kept the second for himself.

"Ready to go?" Dean asked and Sam nodded excitedly beneath his ghost costume.

Sam followed his brother out of the motel room, moving from foot to foot as he waited for Dean to lock the door.

"C'mon, let's go get us some candy!" Dean exclaimed and grabbed Sam's hand and together they crossed the motel parking lot.

 _W_

The brothers had to walk three blocks before they reached a residential area. As they moved closer to the houses and further away from the strip malls and factories, the Winchesters could hear children talking, shouting and laughing.

Turning onto a street with rows of houses on either side, Dean could clearly see kids of varying ages running up and down driveways, dressed in an assortment of costumes, their parents or older siblings following along behind them at a more leisurely pace.

Dean guided Sam to the first house on the right, its grass decorated with plastic gravestones, glow-in-the-dark skeletons hanging from the large maple tree in the middle of the yard and fake spider webs, along with black plastic creepy-crawlies decorating the door.

Stepping up behind a little girl wearing a pink princess dress, shoes and plastic tiara, and who appeared to be her older sister wearing a Cat Woman costume, the Winchester brothers waited patiently for their turn to get candy from the residents.

 _W_

"Dean," Sam tugged at his brother's hand, "I'm tired."

The ten-year old paused and squinted down the current street he and his brother were on. It was an old neighbourhood, with hulking houses and large, stately trees.

It was growing late now and many people had locked their front doors, turned off their front lights and refused to answer for any late-night Trick-Or-Treaters.

"Okay Sammy," Dean said, "Just a couple of more houses and then we'll go home."

The ten-year old slung his nearly overflowing pillowcase over his shoulder and starting down the deserted sidewalk.

"Dean," Sam spoke again, following his brother but now dragging his feet.

"What Sammy?" the older sibling asked.

"I'm scared."

Dean stopped and looked down at his brother. Sam wasn't looking at him. Instead the six-year old was staring down the street.

"Can we go back to the motel now?" Sam asked, now looking up at his brother, "I don't want anymore candy."

Dean, though he wasn't quite ready to leave, sighed and nodded, "Okay, Squirt. C'mon."

The ten-year old turned around and startled at the sight of a figure standing at the corner of the street, a few feet away from the brothers.

The figure was tall and Dean was unable to make out its face because he or she wore a hood or cloak. The figure was holding out a hand, holding a small, round lantern from which an orange flickering glow could be seen.

"Dean," Sam's voice spoke up, "Who is that?"

"I don't know," the ten-year old muttered, "Doesn't matter. C'mon, let's go."

Dean took a couple of steps towards the figure, feeling a sense of unease wash over him as he approached. The figure didn't move from the corner of the street. He (or she) stood in the middle of the sidewalk, silent, facing the brothers.

"He's just trying to scare us," Dean muttered, "Ignore him."

As the brothers moved closer and closer to the figure, the older sibling could now make out more details of the lantern in its hand. The lantern was in fact a root vegetable with its insides carved out, its purple and white skin clearly visible against the orange-red glow of the single piece of coal burning inside it.

A turnip, Dean realized, the asshole's holding a turnip.

The boy's thoughts immediately turned to the story he'd told Sam just hours ago, the legend of Stingy Jack, but he forced himself not to even entertain the idea. Stingy Jack wasn't real, he was just a made up character to scare people at Halloween.

Both Winchesters froze on the spot when a mushy, wheezy voice floated towards them, the speaker sounding as though he were speaking through a mouthful of mud.

"Where do you think you're going?"

Dean scowled and gripped Sam's hand tighter as his brother whimpered in fear.

"Home," the ten-year old snarled, "We're going home. And you're not funny, asshole."

The figure did not reply. Instead it slid its hand into the pocket of its robe and pulled out something large and round and silver.

No, Dean thought; no, this isn't real.

With a flick of its wrist, the figure sent the coin tumbling high into the air.

Dean watched in fascination as the coin dropped, turning end over end, onto the figure's waiting palm.

The figure inclined its head as though reading the coin.

"Dean," Sam said and tugged his brother's hand, "C'mon, please. I'm scared!"

Closing its hand around the coin, the figure began to lift its hand towards it head, moving as though to slid its hood down and reveal its face.

"DEAN!"

The ten-year old tore his attention away from the horrifying figure and began running, nearly dragging his brother down the street, past the figure and towards the safety of further sidewalks.

 _W_

Dean didn't stop running until he and Sam had reached the edge of the residential part of the town. He bent over, hands on his knees, letting his pillowcase slide off his shoulder. Beside him, Sam gasped for air, whimpering fearfully.

Dean straightened himself, "C'mon, we're almost home."

Grabbing his brother's wrist, Dean jogged down the road, wanting only the safety of the motel room.

 _W_

Every two minutes or so, Dean checked the motel room door to make sure it was still locked, peering anxiously through the closed curtains in case the figure had followed them.

The parking lot remained empty and no one tried the door.

Sam was sitting on the end of his bed, legs dangling down, his pillowcase of untouched candy beside him. The ghost costume lay in a crumpled heap in between the two beds.

Dean had thought about calling their Dad and telling him what they had seen but decided against it. The figure had likely only been some asshole teenager who thought it was funny to scare the shit out of kids and of no real danger whatsoever. Besides, Dean and Sam hadn't really been supposed to go out Trick-Or-Treating and the boy didn't want to explain to John how they'd come to see the figure.

"Have some candy, Sammy and then we can go to bed."

The six-year old looked up, his expression telling Dean had hadn't even been listening.

The ten-year old walked across the room, shoved his brother's candy aside and sat down.

"That wasn't real, Sammy," Dean said, trying to convince himself of that fact as well as assure his brother, "It wasn't really him. Just some jerk in a costume trying to scare us."

"Are you sure?" Sam asked, his voice quivering.

"I'm sure," Dean replied and wrapped an arm around his brother's shoulders.

Reaching behind him, the ten-year old grabbed a piece of candy from his brother's pillowcase and opened the bite-sized Tootsie Roll he'd picked.

"That's mine!" Sam exclaimed.

"Yeah, so?" Dean gave his sibling a wry smile.

"Give me one of your candies," Sam demanded.

"No way!" Dean argued, "I'm older so I should get more candy."

Sam spied his sibling's pillowcase sitting on the desk across the room and jumped up.

"Hey! Don't even think about it!" Dean exclaimed, reaching out to grab his sibling and eliciting a happy scream from his brother as he just missed.

"Don't touch my candy!" Dean demanded, a smile spreading across his face as Sam pulled his pillowcase off the desk and dug a hand into it.

"Okay, you asked for it," the ten-year old swiped Sam's candy bag off the bed and shoving his hand into the pillowcase, digging around in it for a prize.

Sam grinned as he pulled out a mini Twix bar and Dean emptied a baggie of gummy worms into his mouth.

 **Author's Note:**

 **Just a little Wee!chester oneshot to get you in the mood for Halloween.**

 **The story of Stingy Jack is a real legend. I just added the part about him tossing the coin and asking passersby where they think they are going, then killing them so they can take his place in either Heaven or Hell.**

 **Please leave a review if you enjoyed.**


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